Estoy de acuerdo utilizamos cookies para mejorar la experiencia de navegación del usuario y para estudiar cómo se utiliza nuestro sitio web. si navega por nuestro sitio web, estará aceptando el uso de las cookies en las condiciones establecidas en la presente política de cookies. esta política puede ser actualizada, por lo que le invitamos a revisarla de forma regular
1,1,1,3,3,3-Hexafluoro-2-propanol is used for preparing hexafluoroalcohol-functionalized methacrylate polymers for lithographic/nanopatterning materials. It plays an important role in the Friedel-Crafts reactions due to its polarity and high ionizing power. It finds use in sample preparation for GCMS. It also catalyzes the epoxidation of cyclooctene and 1-octene with hydrogen peroxide. It is used as a solvent for many reactions and to dissolve peptides. It is also employed to produce high-end chemicals like fluorinated surfactants, fluorinated emulsifier and fluorinated medicine. It acts as a cleaner in electronic industry.
Valuable solvent of high polarity and low nucleophilicity: Tetrahedron Lett., 2335 (1974). Extremely powerful H bond donor but poor H bond acceptor: anions are highly solvated, but cations poorly. For feature article on the use of this unique solvent in the stabilization of radical cations, with particular application to EPR spectroscopy, see: Chem. Commun., 2105 (1996). Preferred solvent for the direct substitution of phenol ethers promoted by [Bis(trifluoroacetoxy)iodo]benzene, L15141: Tetrahedron Lett., 32, 4321 (1991). The intermediacy of radical cations in this reaction has been demonstrated: J. Am. Chem. Soc., 116, 3684 (1994). See also: J. Org. Chem., 60, 7144 (1995).
Powerful solvent for oligopeptides: Bull. Chem. Soc. Jpn., 61, 281 (1984); 66, 494 (1993). Used alone as a peptide coupling medium, HFIP gives poor results, but as a cosolvent along with proton acceptors such as DMF, good results, with improved peptide solubility, can be obtained: Tetrahedron Lett., 33, 7007 (1992).
Effective solvent for uncatalyzed epoxidations of alkenes with H2O2 (caution! 60%): Synlett, 248 (2001); or, more conveniently, Urea hydrogen peroxide adduct, L13940: Eur. J. Org. Chem., 3290 (2002). Superior reaction medium for epoxidations, catalyzed by Hexafluoroacetone trihydrate, L10777: Synlett, 1305 (2001). An efficient, selective oxidation of sulfides to sulfoxides with 30% H2O2 employs HFIP as solvent, avoiding over-oxidation to the sulfone: Tetrahedron Lett., 39, 3141 (1998). For a review of fluorinated alcohols as solvents for selective and clean reactions, see: Synlett, 18 (2004).
The esters formed with N-protected amino acids have been investigated as active intermediates in peptide synthesis: J. Org. Chem., 44, 4577 (1979). See Appendix 6.
The mildly acidic character (pKa 9.3) has been exploited in the selective deprotection of the 4,4'-dimethoxytrityl group in acid-sensitive nucleosides and nucleotides without competing N-glycosyl cleavage: Tetrahedron Lett., 36, 7833 (1995).
Lithiation generates the useful synthon lithium perfluoropropenolate: Org. Synth., 76, 151 (1998):
Pal, U.; Sen, S.; Maiti, N. C. Calpha-H Carries Information of a Hydrogen Bond Involving the Geminal Hydroxyl Group: A Case Study with a Hydrogen-Bonded Complex of 1,1,1,3,3,3-Hexafluoro-2-propanol and Tertiary Amines. J. Phys. Chem. A 2014, 118 (6), 1024-1030.
Wang, L.; Wang, J.-W.; Cui, A.-j.; Cai, X.-X.; Wan, Y.; Chen, Q.; He, M.-Y.; Zhang, W. Regioselective 2,6-dihalogenation of BODIPYs in 1,1,1,3,3,3-hexafluoro-2-propanol and preparation of novel meso-alkyl polymeric BODIPY dyes. RSC Adv. 2013, 3, 9219-9222.
Indicaciones de peligro (UE): H302-H332-H314-H318
Harmful if swallowed. Harmful if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage.
Indicaciones de precaución: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a
Do not breathe dusts or mists. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.